REMOTE ASYMMETRIC INDUCTION - NEW MECHANISTIC INSIGHTS CONCERNING THES-N' AND S-N'' SUBSTITUTION IN ORGANOCOPPER CHEMISTRY

Authors
RAKOTOARISOA H PEREZ RG MANGENEY P ALEXAKIS A
Citation
H. Rakotoarisoa et al., REMOTE ASYMMETRIC INDUCTION - NEW MECHANISTIC INSIGHTS CONCERNING THES-N' AND S-N'' SUBSTITUTION IN ORGANOCOPPER CHEMISTRY, Organometallics, 15(8), 1996, pp. 1957-1959
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear
Journal title
Organometallics → ACNP
ISSN journal
02767333
Volume
15
Issue
8
Year of publication
1996
Pages
1957 - 1959
Database
ISI
SICI code
0276-7333(1996)15:8<1957:RAI-NM>2.0.ZU;2-M
Abstract
The addition of the PhCu, BF3 . Et(2)O reagent to chiral dienic acetal s was studied. The regioselectivity of the reaction was found to be de pendent on the nature of the starting acetal. More importantly, the st ereochemistry of the S(N)2 '' reaction. was found to be opposite to th e one observed for the S(N)2' reaction, Acidic hydrolysis of the resul ting enol ethers afforded the corresponding chiral delta-substituted a ldehydes.